The Bezier tool is better suited to the tasks you're describing. Using 
freehand tool as a precision tool (i.e. for background extraction) is a 
bad idea.
Freehand tool is intended to make coarse selections or tweaks in 
selections that don't need too much precision.
I'd reccomend you this workflow for background extraction:
-Draw a path along the edges of the shape that you want to extract, draw 
other paths for the holes (if you create them in the same path layer 
they are automatically combined with the other paths forming holes).
-Turn path into selection
-Add a mask channel based on that selection.

So, imo, the existence of better tools for the same procedure makes this 
request questionable.
If you ask me, I'd love to have the ability to apply boolean operations 
between different paths before seeing further work on the free selection 

Your other proposal (selection stack) is very interesting, but sounds 
quite difficult tu implement.
I'm not thinking exactly in your examples, but in the possibility to 
transform different selection levels independently (i.e. you selected 3 
circles and you want to adjust the size of the first one).

Oh, btw. I'm experiencing some troubles with SIOX. In some images (I 
couldn't figure it out exactly when it happens) after the initial coarse 
selection the mask is displaced to the lower left of the image (with the 
right shape, but completely misaligned with the image) making it 
impossible to perform the extraction.
Is that a known bug or it's just me?
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